Shop The 100: #3 Ankle Booties

Oh, the ankle bootie. I will admit to being a late adopter of this trend, but I blame the 80s and their silly tiny slouchy boots that made no sense to me. The obvious approach to ankle booties is to wear these under jeans or trousers, the awesome approach is to pair them with skirts and dresses.

2. For pairing with skirts, go mini, but tasteful. The higher the boot comes up on your leg, the shorter the skirt should be – but keep your fashion wits about you, ladies. Let’s not get all “corner of Main Street and ‘Do you need a date tonight?'”

3. Your best friend is a pair of opaque, black tights with a miniskirt and black ankle boots. Again, it’s all about elongating the lines.

Image via The Sartorialist

4. Watch the top of the boot. If it cuts straight across, it may make you look stumpier than you are. I’ve seen it work, even in contrast with the tights or pants (see below), but it can be very hard to pull off that boot shape. It may be safer to find one that is angled in front or more “shoe-like”.

Image via The Sartorialist

5. Ankle booties are a great way to toughen up a flirty dress for a more downtown feeling. It’s not the safe route, but you’re a risk taker. Besides, there is always a pair of pumps waiting for you – so try it a few times for a new, interesting way to remix a dress.

Now is a great time to snap up deals in boots – and, trust me, these will be around next season. It’s a sound wardrobe investment.

Are you an ankle boot girl? (Are you about to be?)

Want to learn more about ankle booties? Of course you do. Pick up a copy of Nina Garcia’s “The One Hundred” for yourself! We’re working our way through all 100 items to assemble the perfectly stylish, workable collection.